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KMID : 1059520080520060663
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Journal of the Korean Chemical Society
2008 Volume.52 No. 6 p.663 ~ p.667
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Synthesis of Pyranobenzopyran Derivatives as a Potent Antibacterial Agent
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Mulwad V. V.
Chaskar Atul C
Langi B. P.
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Abstract
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3-Formyl-4-hydroxy-2H(1)-benzopyran-2-one 1a-d on reaction with diethyl malonate in the presence of piperidine give ethyl-2H,5H-2,5-dioxopyrano[3,2-c] benzopyran-3-oate. 2a-d. Michael addition of 2a-d with ethyl aceto acetate gives ethyl 2,4-dihydroxy-5H, 12H- 5,12-dioxo [2] benzo pyrano [4,3-c] [1] benzopyran- 1-oate (3a-d). 3a-d on Pechmann condensation with ethyl aceto acetate gives 2-acetyl-1,6-dihydroxy-3H,7H,14H-3,7,14-trioxo-pyrano[2/,3/,5,6] [2] benzo pyrano [3,2-c] benzopyran 4a-d. Michael addition followed by cyclisation of acetyl acetone with ethyl-2H,5H- 2,5-dioxo-pyrano[3,2-c] benzopyran-3-oate 2 a-d in the presence of sodium methoxide in boiling methanol afforded1- acetyl-2-methyl-4H,5H,12H,4,5,12-trioxo-dipyrano[3,4-d;3/,2/-c] benzopyran. 5a-d.
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KEYWORD
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3-Formyl-4-hydroxy-2H(1)-benzopyran-2-one, Pyranobenzopyran, Michael Addition, Pechmann Condensation, Antimicrobial Activity
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